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    Awesome sailboat rentals in United States.

    4.9
    (8,496 Reviews)

    Page 33 of 40 • 951 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
    Sailing in Chicago · 12 guests

    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

    New
    $245/hour
    Sailing Lesson in Little River, South Carolina
    Tours in Little River · 1 guest

    Sailing Lesson in Little River, South Carolina

    New
    $360/hour
    40ft Bali Catamaran in Puerto Aventuras near Tulum & Playa del Carmen
    Sailing in Puerto Aventuras · 15 guests

    40ft Bali Catamaran in Puerto Aventuras near Tulum & Playa del Carmen

    New
    $450/hour
    ASA Practice Sailing Exercises | 30ft C&C
    Tours in Manhattan · 6 guests

    ASA Practice Sailing Exercises | 30ft C&C

    New
    $250/hour
    Sail the San Francisco Bay on a Beneteau 45f5 Cruising Monohull
    Sailing in Oakland · 6 guests

    Sail the San Francisco Bay on a Beneteau 45f5 Cruising Monohull

    New
    $200/hour
    40ft Jeanneau Sun Odyssey 42i Crewed Sailboat Charter in Cancún, Quintana Roo
    Sailing in Isla Mujeres · 10 guests

    40ft Jeanneau Sun Odyssey 42i Crewed Sailboat Charter in Cancún, Quintana Roo

    New
    $188+/hour
    Private Sail Up to 13 Guests | 44ft Leopard Catamaran
    Sailing in Saint Michaels · 13 guests

    Private Sail Up to 13 Guests | 44ft Leopard Catamaran

    New
    $580/hour
    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
    Sailing in Key West · 6 guests

    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

    New
    $150/hour
    TRIMARAN "ESCANDALO LATINO" | Your option for a big party at Sea.
    Sailing in Marina Vallarta · 30 guests

    TRIMARAN "ESCANDALO LATINO" | Your option for a big party at Sea.

    New
    $445/hour
    A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6
    Sailing in Sag Harbor · 6 guests

    A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6

    New
    $1,000+/hour
    40ft Luxury Catamaran Private Charter for up to 25 people
    Sailing in Cancún · 25 guests

    40ft Luxury Catamaran Private Charter for up to 25 people

    New
    Superowner
    $357+/hour
    Charter 39ft 'Two J Birds' Beneteau Sailboat In Kemah, Texas
    Sailing in Seabrook · 8 guests

    Charter 39ft 'Two J Birds' Beneteau Sailboat In Kemah, Texas

    New
    $82+/hour
    Bahamas Sunset Cruise
    Powerboats in Nassau · 8 guests

    Bahamas Sunset Cruise

    New
    $350/hour
    Exclusive Ocean Cruise
    Sailing in Long Beach · 12 guests

    Exclusive Ocean Cruise

    New
    $250/hour
    Deal of the Week! All-Inclusive Leopard 51Ft Catamaran in Cancun, Mexico.
    Powerboats in Cancún · 25 guests

    Deal of the Week! All-Inclusive Leopard 51Ft Catamaran in Cancun, Mexico.

    New
    Superowner
    Best of 2026
    $572/hour
    Oceanis 43 Sailing Yacht in Seabrook, Texas
    Sailing in Seabrook · 10 guests

    Oceanis 43 Sailing Yacht in Seabrook, Texas

    New
    $175/hour
    Charter 40ft Norseman Catamaran in Kemah, Texas!
    Sailing in Seabrook · 12 guests

    Charter 40ft Norseman Catamaran in Kemah, Texas!

    New
    $331/hour
    100ft Turkish Gulet Sailing Boat in Cabo San Lucas, Baja California Sur
    Sailing in Marina · 40 guests

    100ft Turkish Gulet Sailing Boat in Cabo San Lucas, Baja California Sur

    New
    $1,200/hour
    42ft Jeanneau Sailboat For Rent in Cancun, Quintana Roo
    Sailing in Isla Mujeres · 12 guests

    42ft Jeanneau Sailboat For Rent in Cancun, Quintana Roo

    New
    $163/hour
    Luxury Sailboat in Panama for Pearl Islands or Taboga
    Sailing in Panama City · 20 guests

    Luxury Sailboat in Panama for Pearl Islands or Taboga

    New
    $600/hour
    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale
    Sailing in Fort Lauderdale · 12 guests

    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale

    New
    $375/hour
    Sausalito: 41ft Jeanneau 410 Sun Odyssey Sailing Charter for Up to 10 Guests
    Sailing in Sausalito · 10 guests

    Sausalito: 41ft Jeanneau 410 Sun Odyssey Sailing Charter for Up to 10 Guests

    New
    $415/hour
    Catamaran with Underwater Viewing Pods for 5-Star Whale Watching in Dana Point
    Tours in Dana Point · 49 guests

    Catamaran with Underwater Viewing Pods for 5-Star Whale Watching in Dana Point

    New
    $1,625/hour
    Cheers to the Seas: 37ft Catamaran Charter in Cancún with Open Bar Options!
    Sailing in Cancún · 25 guests

    Cheers to the Seas: 37ft Catamaran Charter in Cancún with Open Bar Options!

    New
    Superowner
    $165+/hour

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